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12 Cards in this Set

  • Front
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Aromatic Definition

Aliphatic Definition
- cyclic, conjugated polyenes
> with 4n + 2 pi electrons, adopt planar conformations.

- all compounds that are not aromatic
Huckels rule
- 4n + 2 pi electrons = aromatic
Aromatic Reactions:

2 types
- Electrophilic Aromatic Substitution

- Reduction
Aromatic Reactions: Electrophilic Aromatic Substitutions

4 types
- Halogenation

- Sulfonation

- Nitration

- Acylation (Friedel-Crafts Reaction)
Electrophilic Aromatic Sub: Halogenation

what is the reactant? what is the catalyst/solvent?
- occurs with molecular Br or Cl in presence of lewis acid (i.e. FeBr3, FeCl3, AlCl3)

- product is a mono-substituted benzene.
Electrophilic Aromatic Sub: Sulfonation
- react with fuming sulfuric acid (SO3/H2SO4)

- Forms sulfonic acid
Electrophilic Aromatic Sub: Nitration
- uses H2SO4/HNO3 to add nitro group.

- makes nitro compound
Electrophilic Aromatic Sub: Acylation

what lewis acid is used for this synthesis to complete?
- carbocation electrophile, usually an acyl group, incorporates into aromatic ring.

- AlCl3 is used in addition
Substituent Effects

whats the difference between activating and deactivating?
- substitution is enhanced when an activating substituent present.

- substitution inhibited when deactivating substituent present.
Substituent Effects: Activating Substituents

1 type
- Activating ortho/para-directing substituents (e- donating)
>All amino groups (Except NO2), alkoxy, alcohol, -O(basically whenever O is directly attached, regardless of things also attached to O).
Substituent Effects: Deactivating Substituents

2 types
- Deactivating Ortho/para directing substituents (weakly e- withdrawing.
> (Think HALOGENS) F, Cl, I, Br

- Deactivating Meta-directing substituents (e- withdrawing)
>NO2, Sulfuric Acid, Carbonyl compounds (Carboxy acids, esters, aldehyde, acetone.
Reactions: Reduction

1 type

reaction: Whats used in it? whats the product?
- Catalytic Reduction, (Rh catalyst)

- benzene >>>(H2, Rh/C / hot temp)>>> Cyclohexane